For his second act, he has transplanted a fledgling personal shopping service for men, Trunk Club, from the West Coast to Chicago's artsy River North neighborhood.

Chicago as hog butcher and steel-maker for the nation? Not so much anymore.

Since taking office in 1989, Mayor Richard Daley has hauled Chicago into the information age and made it a greener and more sophisticated place to live and work. This month he received a hearty pat on the back for his economic development efforts from two of the world's prestigious think tanks: the Brookings Institution and the London School of Economics and Political Science.

"He has done an absolutely remarkable job," former Brookings board member James Johnson said, in presenting Daley with the organizations' Global Metro Award.

Yet, while no one would deny Daley his due — the central city is among the nation's most vibrant, the economy is more diversified and cultural offerings have blossomed — observers say Chicago's robust performance of the 1990s has slackened in the past decade and now is seriously stalled.

The outlook can best be described as murky as unemployment rates have outstripped the national average during the downturn, the once-bubbly commercial and residential real estate markets remain battered, and city government edges ever closer to a full-blown financial crisis, a status already crippling the state.

The region also has lagged in innovation, firm creation and growth in productivity and gross metropolitan product over the past decade, according to economic development consultant Robert Weissbourd, president of RW Ventures LLC.

Daley's two long-held dreams of Chicago emerging as a high-tech center and a global business center remain just out of reach.

Chicago ranked seventh in 2009 tech employment among U.S. cities, having lost 8,200 jobs that year, according to the TechAmerica Foundation. And a report by Chicago Federal Reserve Bank economist William Testa suggests the city's economy remains largely tied to its traditional Midwestern business partners.

"We haven't made the real global jump yet, and we have not made the tech jump either, but we are finally poised," said Paul O'Connor, who for many years ran World Business Chicago, the city's economic development affiliate. "We are still a major contender, but, yeah, we can blow it."

Or, as Testa put it, "Given the poor performance of this decade, we need to rethink the challenges for Chicago."

Rita Athas, president of World Business Chicago, argues for a brighter outlook, noting that the city has been recognized as a global city by a number of organizations and that the meteoric rise of Chicago-born daily deal site Groupon will lead to greater recognition of the city's emerging tech base.

"The foundation the mayor laid is really serving us well," she said.

And, indeed, Chicago arrives at this turning point with some critical economic underpinnings working in its favor.

The mayor's firmly forged alliance with the city's business elite, as well as his liberal use of conventional economic development tools, from earmarking property-tax growth for infrastructure development to crafting incentive packages to land corporate headquarters, have helped the city move beyond its smokestack roots and more deeply into business, professional and technical services.

And with Millennium Park as its crown jewel, downtown has expanded southward and westward, with the central city becoming home to a youthful, educated work force. Thirty-one percent of the city's population had a bachelor's degree in 2008, up from 19.5 percent in 1990.

"That stuff is hugely valuable to me," said 33-year-old entrepreneur Spaly, who moved Trunk Club, an online men's outfitter, from Bend, Ore., to River North late last year.

His investors suggested New York or San Francisco, but the Midwest native chose Chicago, and not just because of lower rents and salary levels.

"There are scores of young, talented, hardworking people living within blocks of the office; it's awesome," said Spaly, who lives nearby himself. The startup has hired 20 workers, all younger than Spaly, and the company hopes to reach $5 million in sales next year.

Eric Lefkofsky, co-founder of Groupon, the city's first truly highflying tech startup, said Chicago has the ingredients for nurturing new companies, from a sophisticated work force and top-rated universities to willing investors, but it lacks confidence.

"You go to New York, and there's nothing that city doesn't think it can achieve," he said. "You go to Silicon Valley, and they think everything there is cutting edge. And Boston thinks they are smarter than everyone.